In my last post, I wrote about asking a woman out [link]. Today, I’d like to talk about actually planning your date.
Good dates are not random events. Planning a date is a skill that gentlemen master – a skill that can significantly increase the likelihood that you and your date connect. Here are a few of my tips for planning dates:
- Think of a date as an event you’re hosting. You’ll want to plan, think things through, and make sure your guest is comfortable.
- Choose somewhere that gives a glimpse into your life: since women are always interpreting, choose a place that says something about you. Choose a bar you enjoy, a bookstore you love, an activity that is your hobby. Make sure your date planning says something about you and that it’s something attractive. It’s better to show her who you are than to plan something fancy that doesn’t resemble your everyday life.
- Take her somewhere she’s never been before. If you take her to the same place other men have taken her, you’re already appearing to be like every other guy she’s dated. This means that, in your spare time, you should find a handful of spots that women you date probably haven’t been to.
- Set a very clear and easy meeting place.
- Have a nearby place to hang out while you wait for her to arrive. You should be ready for your date to be late – and you don’t want to be waiting there for her. Instead, tell her you’ll be nearby and that she should text you when she arrives. Hang out at a nearby place where you can kill time. Then, when she texts, you will be at a conveniently close location and can walk or drive over in a few minutes; this shows that you have your own life you’re living and, if she’s late, she’s not going to see you as the guy who’s been waiting there for 15 minutes with nothing better to do.
- Plan three locations over the course of the night. Psychology studies report that people feel much closer when they’ve been to multiple locations together. How long you spend at each is not as important. You could start with an art gallery (free, plenty to discuss, can be done in 20 minutes), then go for a drink, and then switch locations for a nightcap. By the end of the night, it almost feels like three dates.
- Choose places that allow you to sit side-by-side or diagonal. Don’t take a date somewhere you must sit across the table from her. It makes it difficult to touch her playfully and practically impossible to kiss her. Find venues that have couches where you can sit comfortably side by side.
- Your locations should be arranged chronologically to increase intimacy. Don’t start at a dark candlelit bar sitting next to each other and then transition to a bright public space with lots of people around. The idea of a date is to sink into each other. As you’ll see in the next post on the date itself, you’ll want to make sure that the last location is conducive to the two of you kissing discretely.
- Last, think of what the woman will need to wear. If you’re taking her somewhere fancy where she may be wearing heels, don’t then plan something where she needs to walk around a museum in uncomfortable shoes. Women think about this. You should too.
With these basics, you should be able to plan a three-venue date that increases intimacy, gets you talking and touching, and leads to the kind of date you’ll both want more of.
Once you’ve mastered the blueprint for flirting, you’ll start seeing many opportunities to ask your woman out on a date. Whether you met online or offline, asking her out is an important step that you’ll want to master.
Here are a few tips:
- Don’t ask a woman out until you’re relatively certain she’s going to say yes. Keep flirting until you can tell that she’s attracted to you and comfortable with you.
- If you happen to have a pre-existing relationship with her (friends, co-workers, etc.), make it 100% explicitly clear that this is a romantic date. It’s better to have her say no than be stuck in an ambiguous friend zone.
- Ask her out for a specific day and time. The activity can be as simple as “let’s get a drink” – though my next post will talk about planning an excellent date.
- When you invite her out, make it clear that you have an active social calendar (which you should!) but that you’re interested in seeing her:
- “I’m going to a gallery opening on Thursday and seeing a movie with friends on Saturday, but if you’re free on Friday or Sunday we should grab a drink….”
- Use suggestions rather than questions when you’re asking a woman out – it communicates that you’re leading and not begging:
- Using “Let’s”: “If you’re free Thursday night, let’s go to the….”
- Using “We should: “I know you mentioned cooking this weekend. If you’re not exhausted by being Martha Stewart, we should go to…on Sunday.”
- She might be busy on the day you propose. If she’s interested in seeing you, she’ll often propose another date. This is a good sign.
- If she doesn’t propose another date, flirt more (over the course of another day or two) before you invite her out again.
- If she is always busy and never proposes a new date, it’s best to ask her feelings outright: “Hey, you seem cool and I’d like us to hang out and get to know each other better. But you seem busy. Are you interested in hanging out?” If she says yes, you can ask her, “What’s the best way to make this happen?” Then she’s participating in the invitation. If she says no, then you’ve clarified your situation and can move on.
- Once she accepts the date, send her a reminder the day before that’s fun: “When I see you tomorrow night, I expect us to run into each other’s arms like the ending of a romantic movie. Anything less will be very disappointing.”
With these tips, you should be successfully asking women out to set up dates. In my next post, I’ll be talking about how to plan a date that you’ll both remember.
A friend of mine recently showed me his online conversations with women and asked me what I thought. He was good at the basic skills of banter (which I wrote about earlier) but his conversations would devolve into exchanging facts – and women would soon grow bored and respond less often. What he was missing was the act of interpretation.
For women, all flirting in the early stages is really about one thing: she’s interpreting the things you do and say to figure out what kind of guy are you? What are you made of? Are you fun? Are you ambitious? Are you honorable? Do you appreciate sensual pleasures enough to please her in bed? Will it be awkward if she introduces you to her friends? Are you a gentleman? Will you be fun at first and then later be unreliable?
Women approach dating the way men approach investing: they scrutinize everything for clues about the future before they jump in. For women, flirting is a constant state of interpreting what you show her. Further, it goes both ways: they carefully do and say certain things so that you interpret who they are (and want to date them). This desire to see the future is based on not wanting to waste their time or be hurt. It’s why fortune tellers and horoscopes are so powerful for women: they promise to interpret something hidden and reveal what the future might look like.
How to Connect
The correct interpretation of what a woman is really telling you, as well as telling stories she can interpret in your favor, creates opportunities for a gentleman to connect with a woman. Here are my tips:
- When she tells you a fact about herself, try to interpret it yourself. If she tells you she loves bungee jumping, don’t tell your own story about bungee jumping. Ask her if she likes taking risks. Interpret what she’s telling you and you’ll find yourself connecting very quickly.
- After you interpret something she says/does, don’t assume you got it right. Ask her if she likes taking risks. Don’t tell her, “I knew you were the kind of person who likes to take risks.” It cuts off conversation – and you might be wrong.
- Tell her stories from your life that she can interpret to understand who you are – not just random stories to keep the conversation going.
- Interpret your own stories for her. In my blog post about creating stories I talk about how to do this.
- With practice, you can jokingly misinterpret what she tells you. If she tells you she went to graduate school but doesn’t mention what she studied, you can say something like, “I’m going to assume that was graduate school to become a secret agent. Do you look good in a ninja outfit?” This can be very risky online because there’s little context – if it’s not over-the-top outrageous and obviously a joke, she may take you seriously. It’s also complicated when you’re crossing cultural and linguistic boundaries, like with women in Russia, for instance they seem so serious, but can melt and laugh so easily. So proceed carefully, but see if you can find ways to interpret in funny ways.
- When you interpret something she tells you into a personality trait of hers – and it’s a trait you respect – tell her so. Something as simple as “I respect that” or “I think that’s awesome” can really help build a connection. She will like this because this is a compliment that she earned – not just you saying she’s pretty.
Once you understand the underlying nature of flirting as constant two-way interpretation, you start to see conversations differently. And, like my friend is finding since our conversation, interpretation gets you beyond exchanging facts and into real connection.